#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/49/4034905.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4034905
loop_
_publ_author_name
'Mir, Roya'
'Dudding, Travis'
_publ_section_title
;
 Bis(amino)cyclopropenium Trifluoroborates: Synthesis, Hydrolytic
 Stability Studies, and DFT Insights.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4384
_journal_page_last               4388
_journal_paper_doi               10.1021/acs.joc.8b00060
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C15 H28 B F3 N2'
_chemical_formula_sum            'C15 H28 B F3 N2'
_chemical_formula_weight         304.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6198(4)
_cell_length_b                   13.9656(4)
_cell_length_c                   9.6933(3)
_cell_measurement_reflns_used    9324
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.43
_cell_measurement_theta_min      2.56
_cell_volume                     1708.38(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25360
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.126
_diffrn_reflns_theta_min         2.558
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_correction_T_min  0.9530
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.271
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
; 
 Flack x determined using 2161 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.08(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         5919
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0706P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                5180
_reflns_number_total             5919
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b00060_si_002.cif
_cod_data_source_block           rm11976_a
_cod_database_code               4034905
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.63635(10) 0.79338(9) 0.37729(13) 0.0241(2) Uani 1 1 d . .
N2 N 0.51334(10) 0.66488(8) 0.67210(12) 0.0232(2) Uani 1 1 d . .
C1 C 0.62636(11) 0.71631(10) 0.45494(14) 0.0206(2) Uani 1 1 d . .
C2 C 0.57984(11) 0.66841(9) 0.56676(14) 0.0199(2) Uani 1 1 d . .
C3 C 0.65892(11) 0.62456(9) 0.49004(14) 0.0203(2) Uani 1 1 d . .
C4 C 0.72237(12) 0.79941(11) 0.27270(16) 0.0263(3) Uani 1 1 d . .
H4A H 0.7215 0.8659 0.2343 0.032 Uiso 1 1 calc R U
C5 C 0.83100(13) 0.78352(12) 0.3372(2) 0.0341(4) Uani 1 1 d . .
H5A H 0.8856 0.7880 0.2656 0.051 Uiso 1 1 calc R U
H5B H 0.8438 0.8325 0.4077 0.051 Uiso 1 1 calc R U
H5C H 0.8335 0.7199 0.3797 0.051 Uiso 1 1 calc R U
C6 C 0.70221(19) 0.73084(15) 0.15331(19) 0.0441(5) Uani 1 1 d . .
H6A H 0.7599 0.7362 0.0860 0.066 Uiso 1 1 calc R U
H6B H 0.6989 0.6651 0.1883 0.066 Uiso 1 1 calc R U
H6C H 0.6349 0.7471 0.1088 0.066 Uiso 1 1 calc R U
C7 C 0.56696(13) 0.87817(11) 0.40252(18) 0.0293(3) Uani 1 1 d . .
H7A H 0.5050 0.8554 0.4577 0.035 Uiso 1 1 calc R U
C8 C 0.62356(17) 0.95301(13) 0.4885(2) 0.0424(4) Uani 1 1 d . .
H8A H 0.5764 1.0078 0.5035 0.064 Uiso 1 1 calc R U
H8B H 0.6435 0.9253 0.5777 0.064 Uiso 1 1 calc R U
H8C H 0.6874 0.9744 0.4399 0.064 Uiso 1 1 calc R U
C9 C 0.52331(14) 0.91869(15) 0.2676(2) 0.0418(4) Uani 1 1 d . .
H9A H 0.4782 0.9741 0.2876 0.063 Uiso 1 1 calc R U
H9B H 0.5822 0.9385 0.2083 0.063 Uiso 1 1 calc R U
H9C H 0.4815 0.8694 0.2205 0.063 Uiso 1 1 calc R U
C10 C 0.44935(14) 0.74892(11) 0.71396(17) 0.0317(3) Uani 1 1 d . .
H10A H 0.4537 0.7971 0.6378 0.038 Uiso 1 1 calc R U
C11 C 0.4960(2) 0.79485(15) 0.8428(3) 0.0568(6) Uani 1 1 d . .
H11A H 0.4530 0.8503 0.8693 0.085 Uiso 1 1 calc R U
H11B H 0.4964 0.7481 0.9182 0.085 Uiso 1 1 calc R U
H11C H 0.5687 0.8157 0.8238 0.085 Uiso 1 1 calc R U
C12 C 0.33307(15) 0.72340(16) 0.7334(2) 0.0431(5) Uani 1 1 d . .
H12A H 0.2935 0.7807 0.7610 0.065 Uiso 1 1 calc R U
H12B H 0.3043 0.6987 0.6465 0.065 Uiso 1 1 calc R U
H12C H 0.3265 0.6744 0.8052 0.065 Uiso 1 1 calc R U
C13 C 0.51375(11) 0.57861(10) 0.76198(15) 0.0239(3) Uani 1 1 d . .
H13A H 0.4637 0.5913 0.8399 0.029 Uiso 1 1 calc R U
C14 C 0.62290(14) 0.56117(12) 0.82488(16) 0.0307(3) Uani 1 1 d . .
H14A H 0.6205 0.5040 0.8834 0.046 Uiso 1 1 calc R U
H14B H 0.6748 0.5517 0.7510 0.046 Uiso 1 1 calc R U
H14C H 0.6435 0.6167 0.8807 0.046 Uiso 1 1 calc R U
C15 C 0.47171(14) 0.49160(12) 0.68376(17) 0.0317(3) Uani 1 1 d . .
H15A H 0.4726 0.4355 0.7445 0.048 Uiso 1 1 calc R U
H15B H 0.3990 0.5041 0.6533 0.048 Uiso 1 1 calc R U
H15C H 0.5166 0.4794 0.6032 0.048 Uiso 1 1 calc R U
B1 B 0.74211(13) 0.53551(12) 0.46794(18) 0.0233(3) Uani 1 1 d . .
F1 F 0.83496(8) 0.55702(7) 0.54089(13) 0.0385(3) Uani 1 1 d . .
F2 F 0.69848(9) 0.45039(6) 0.51899(12) 0.0369(2) Uani 1 1 d . .
F3 F 0.76590(9) 0.52419(8) 0.32892(10) 0.0365(2) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C7 119.84(12)
C1 N1 C4 120.30(12)
C7 N1 C4 119.65(11)
C2 N2 C10 121.86(12)
C2 N2 C13 118.72(11)
C10 N2 C13 118.90(11)
N1 C1 C3 149.84(13)
N1 C1 C2 150.45(13)
C3 C1 C2 59.61(10)
N2 C2 C3 148.64(13)
N2 C2 C1 151.65(13)
C3 C2 C1 59.67(9)
C1 C3 C2 60.71(9)
C1 C3 B1 148.95(13)
C2 C3 B1 149.84(12)
N1 C4 C5 111.65(13)
N1 C4 C6 111.11(13)
C5 C4 C6 111.74(15)
N1 C4 H4A 107.4
C5 C4 H4A 107.4
C6 C4 H4A 107.4
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C4 C6 H6A 109.5
C4 C6 H6B 109.5
H6A C6 H6B 109.5
C4 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N1 C7 C8 111.14(14)
N1 C7 C9 111.42(14)
C8 C7 C9 112.65(14)
N1 C7 H7A 107.1
C8 C7 H7A 107.1
C9 C7 H7A 107.1
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N2 C10 C12 111.96(15)
N2 C10 C11 110.33(15)
C12 C10 C11 111.73(16)
N2 C10 H10A 107.5
C12 C10 H10A 107.5
C11 C10 H10A 107.5
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
N2 C13 C14 111.51(12)
N2 C13 C15 110.64(12)
C14 C13 C15 112.63(13)
N2 C13 H13A 107.3
C14 C13 H13A 107.3
C15 C13 H13A 107.3
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C13 C15 H15A 109.5
C13 C15 H15B 109.5
H15A C15 H15B 109.5
C13 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
F3 B1 F2 109.33(13)
F3 B1 F1 109.46(13)
F2 B1 F1 109.42(13)
F3 B1 C3 110.54(12)
F2 B1 C3 110.21(12)
F1 B1 C3 107.85(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3195(17)
N1 C7 1.4928(19)
N1 C4 1.4877(18)
N2 C2 1.3226(17)
N2 C10 1.4813(19)
N2 C13 1.4868(17)
C1 C3 1.3879(19)
C1 C2 1.4025(18)
C2 C3 1.3871(19)
C3 B1 1.642(2)
C4 C5 1.523(2)
C4 C6 1.524(3)
C4 H4A 1.0000
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 C8 1.516(3)
C7 C9 1.527(2)
C7 H7A 1.0000
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 C12 1.522(3)
C10 C11 1.523(3)
C10 H10A 1.0000
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 C14 1.526(2)
C13 C15 1.527(2)
C13 H13A 1.0000
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
B1 F3 1.3896(19)
B1 F2 1.4004(18)
B1 F1 1.4012(19)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7 N1 C1 C3 -178.0(2)
C4 N1 C1 C3 -3.2(3)
C7 N1 C1 C2 -4.1(3)
C4 N1 C1 C2 170.7(2)
C10 N2 C2 C3 172.5(2)
C13 N2 C2 C3 0.8(3)
C10 N2 C2 C1 -3.7(4)
C13 N2 C2 C1 -175.3(2)
N1 C1 C2 N2 1.2(5)
C3 C1 C2 N2 177.7(3)
N1 C1 C2 C3 -176.4(3)
N1 C1 C3 C2 176.5(3)
N1 C1 C3 B1 4.5(4)
C2 C1 C3 B1 -172.0(3)
N2 C2 C3 C1 -177.9(3)
N2 C2 C3 B1 -6.1(4)
C1 C2 C3 B1 171.8(3)
C1 N1 C4 C5 -55.61(18)
C7 N1 C4 C5 119.18(15)
C1 N1 C4 C6 69.87(18)
C7 N1 C4 C6 -115.33(17)
C1 N1 C7 C8 98.13(17)
C4 N1 C7 C8 -76.70(18)
C1 N1 C7 C9 -135.34(14)
C4 N1 C7 C9 49.84(19)
C2 N2 C10 C12 131.18(15)
C13 N2 C10 C12 -57.21(19)
C2 N2 C10 C11 -103.70(18)
C13 N2 C10 C11 67.91(19)
C2 N2 C13 C14 57.83(18)
C10 N2 C13 C14 -114.05(16)
C2 N2 C13 C15 -68.36(17)
C10 N2 C13 C15 119.76(16)
C1 C3 B1 F3 -40.1(3)
C2 C3 B1 F3 153.8(2)
C1 C3 B1 F2 -161.1(2)
C2 C3 B1 F2 32.8(3)
C1 C3 B1 F1 79.5(3)
C2 C3 B1 F1 -86.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139113261
